Synthesis, Cytotoxic Activity, Crystal Structure, DFT, Molecular Docking Study of <i>β</i>-Enaminonitrile Incorporating 1<i>H</i>-Benzo[<i>f</i>]Chromene Moiety
In this work, we used microwave irradiation conditions to synthesize <i>β</i>-enaminonitrile (<b>4</b>), which was affirmed using single crystal X-ray diffraction and the different spectral data. Two tumor cell lines, MCF-7 and MCF-7/ADR, as well as two normal cell lines, HFL...
| Main Authors: | , , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-12-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/13/1/24 |
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| author | Mosa H. Alsehli Lali M. Al-Harbi Rawda M. Okasha Ahmed M. Fouda Hazem A. Ghabbour Abd El-Galil E. Amr Ahmed A. Elhenawy Ahmed M. El-Agrody |
| author_facet | Mosa H. Alsehli Lali M. Al-Harbi Rawda M. Okasha Ahmed M. Fouda Hazem A. Ghabbour Abd El-Galil E. Amr Ahmed A. Elhenawy Ahmed M. El-Agrody |
| author_sort | Mosa H. Alsehli |
| collection | DOAJ |
| description | In this work, we used microwave irradiation conditions to synthesize <i>β</i>-enaminonitrile (<b>4</b>), which was affirmed using single crystal X-ray diffraction and the different spectral data. Two tumor cell lines, MCF-7 and MCF-7/ADR, as well as two normal cell lines, HFL-1 and WI-38, were used to assess the anticancer activity of compound <b>4</b>. The studied molecule exhibited potent efficacy against the MCF-7 and MCF-7/ADR cell lines compared with the reference drugs. Furthermore, target compound <b>4</b> had feeble activity against HFL-1 and WI-38. The chemical reactivity was discussed using DFT and QTAIM analysis to study the intrinsic electronic properties of compound <b>4</b>. A molecular docking study was also conducted to examine their binding affinity to the EGFR. Compound <b>4</b> revealed a stable binding mode at the enzyme active pocket more than the reference inhibitor. The docking analysis was performed for molecule (<b>4</b>). |
| first_indexed | 2024-03-09T13:06:17Z |
| format | Article |
| id | doaj.art-04f4aabaea1d4f869c164a683caf63cf |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-09T13:06:17Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-04f4aabaea1d4f869c164a683caf63cf2023-11-30T21:46:57ZengMDPI AGCrystals2073-43522022-12-011312410.3390/cryst13010024Synthesis, Cytotoxic Activity, Crystal Structure, DFT, Molecular Docking Study of <i>β</i>-Enaminonitrile Incorporating 1<i>H</i>-Benzo[<i>f</i>]Chromene MoietyMosa H. Alsehli0Lali M. Al-Harbi1Rawda M. Okasha2Ahmed M. Fouda3Hazem A. Ghabbour4Abd El-Galil E. Amr5Ahmed A. Elhenawy6Ahmed M. El-Agrody7Department of Chemistry, College of Science, Taibah University, Al Medina Al Munawwara 30002, Saudi ArabiaChemistry Department, Faculty of Science, King Abdul-Aziz University, Jeddah 21589, Saudi ArabiaChemistry Department, College of Science, Taibah University, Medina 30002, Saudi ArabiaChemistry Department, Faculty of Science, King Khalid University, Abha 61413, Saudi ArabiaDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, EgyptApplied Organic Chemistry Department, National Research Center, Dokki, Giza 12622, EgyptChemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo 11884, EgyptChemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo 11884, EgyptIn this work, we used microwave irradiation conditions to synthesize <i>β</i>-enaminonitrile (<b>4</b>), which was affirmed using single crystal X-ray diffraction and the different spectral data. Two tumor cell lines, MCF-7 and MCF-7/ADR, as well as two normal cell lines, HFL-1 and WI-38, were used to assess the anticancer activity of compound <b>4</b>. The studied molecule exhibited potent efficacy against the MCF-7 and MCF-7/ADR cell lines compared with the reference drugs. Furthermore, target compound <b>4</b> had feeble activity against HFL-1 and WI-38. The chemical reactivity was discussed using DFT and QTAIM analysis to study the intrinsic electronic properties of compound <b>4</b>. A molecular docking study was also conducted to examine their binding affinity to the EGFR. Compound <b>4</b> revealed a stable binding mode at the enzyme active pocket more than the reference inhibitor. The docking analysis was performed for molecule (<b>4</b>).https://www.mdpi.com/2073-4352/13/1/24β-enaminonitrilemicrowave irradiationX-rayantitumor activitydocking study |
| spellingShingle | Mosa H. Alsehli Lali M. Al-Harbi Rawda M. Okasha Ahmed M. Fouda Hazem A. Ghabbour Abd El-Galil E. Amr Ahmed A. Elhenawy Ahmed M. El-Agrody Synthesis, Cytotoxic Activity, Crystal Structure, DFT, Molecular Docking Study of <i>β</i>-Enaminonitrile Incorporating 1<i>H</i>-Benzo[<i>f</i>]Chromene Moiety Crystals β-enaminonitrile microwave irradiation X-ray antitumor activity docking study |
| title | Synthesis, Cytotoxic Activity, Crystal Structure, DFT, Molecular Docking Study of <i>β</i>-Enaminonitrile Incorporating 1<i>H</i>-Benzo[<i>f</i>]Chromene Moiety |
| title_full | Synthesis, Cytotoxic Activity, Crystal Structure, DFT, Molecular Docking Study of <i>β</i>-Enaminonitrile Incorporating 1<i>H</i>-Benzo[<i>f</i>]Chromene Moiety |
| title_fullStr | Synthesis, Cytotoxic Activity, Crystal Structure, DFT, Molecular Docking Study of <i>β</i>-Enaminonitrile Incorporating 1<i>H</i>-Benzo[<i>f</i>]Chromene Moiety |
| title_full_unstemmed | Synthesis, Cytotoxic Activity, Crystal Structure, DFT, Molecular Docking Study of <i>β</i>-Enaminonitrile Incorporating 1<i>H</i>-Benzo[<i>f</i>]Chromene Moiety |
| title_short | Synthesis, Cytotoxic Activity, Crystal Structure, DFT, Molecular Docking Study of <i>β</i>-Enaminonitrile Incorporating 1<i>H</i>-Benzo[<i>f</i>]Chromene Moiety |
| title_sort | synthesis cytotoxic activity crystal structure dft molecular docking study of i β i enaminonitrile incorporating 1 i h i benzo i f i chromene moiety |
| topic | β-enaminonitrile microwave irradiation X-ray antitumor activity docking study |
| url | https://www.mdpi.com/2073-4352/13/1/24 |
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